Difluoromethylenephosphonates: synthesis and transformations

Chunikhin, K. S.; Kadyrov, A. A.; Pasternak, P. V.; Чкаников, Н. Д.

doi:10.1070/rc2010v079n05abeh003883

Cited by 23 publications

(14 citation statements)

References 19 publications

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“…First, it should be expected to significantly decrease the acidity of the phosphorus-containing acid function moving from a phosphate to a phosphonate moiety. [18] The geometric properties of the (difluoromethyl)phosphonates are similar to those of the phosphate. [19] Compound 1 was synthesized by Unger in 1978 and tested in vitro on isolated Kdo8P synthase.…”

Section: Resultsmentioning

confidence: 97%

“…Key biosynthetic steps involved in Kdo production and possible targets for A5P phosphonate analogues. [18] In fact, the -CF 2 -group is an isoelectronic and isosteric analogue of the oxygen atom. First, it should be expected to significantly decrease the acidity of the phosphorus-containing acid function moving from a phosphate to a phosphonate moiety.…”

Section: Resultsmentioning

confidence: 99%

“…its ability to resist enzymatic and chemical hydrolysis. [18] Some of these derivatives were found to be potent inhibitors of several enzymes and proved to be important mechanistic probes for numerous biological processes involving phosphates. This is attributable to the introduction of an electron-donating alkyl group, resulting in a different dissociation state for the analogue compared to the natural compound at physiological pH.…”

Section: Resultsmentioning

confidence: 99%

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Phosphonate Analogues of Arabinose 5‐Phosphate: Putative Ligands for Arabinose 5‐Phosphate Isomerases

Gabrielli¹,

Airoldi²,

Sperandeo³

et al. 2013

Eur J Org Chem

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Metabolically stable arabinose 5‐phosphate analogues possessing phosphate mimetic groups at the 5‐position were synthesized and evaluated by saturation‐transfer‐difference (STD) NMR studies for their ability to interact with arabinose 5‐phosphate isomerase. Isosteric methylphosphonate 1 and (difluoromethyl)phosphonate 3 were recognised and bound by the catalytic pocket of the enzyme. The synthesized compounds were tested in vivo on E. coli and P. aeruginosa strains in order to evaluate their antibacterial activity.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Phosphonate Analogues of Arabinose 5‐Phosphate: Putative Ligands for Arabinose 5‐Phosphate Isomerases

Gabrielli¹,

Airoldi²,

Sperandeo³

et al. 2013

Eur J Org Chem

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“…In particular, nucleoside alkyl phosphonate esters are generally more stable to nucleases and have greater cell permeability . Blackburn and Kent suggested that α‐fluoro and α,α‐difluoromethylphosphonate mimic phosphate esters are better than the corresponding phosphonates . This assumption was based on electronic and steric considerations.…”

Section: Introductionmentioning

confidence: 99%

The Synthesis of Novel 5′‐Deoxy‐3′,5′,5′‐trifluoro‐apiosyl Nucleoside Phosphonic Acid Analogs as Antiviral Agents

Kim

Hong

2015

Bulletin Korean Chem Soc

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“…10 In particular, this frag ment is thought to be an isopolar and isosteric substitute for oxygen. 11 Some CF 2 containing compounds exhibit high physiological activity, 12 including antitumor 13 and antifungal effects 14 and inhibition of HIV 1 reverse tran scriptase 15 and various protein kinases. 16 Thus, develop ment of synthetic routes to compounds with functional ized fragments CF 2 is an important step in searching for novel biologically active molecules.…”

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confidence: 99%

Synthesis of new fluorine-containing pyrazolo[3,4-b]pyridinones as promising drug precursors

et al. 2011

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Methods for the synthesis of 4 R 6,7 dihydro 1H pyrazolo[3,4 b]pyridin 6 ones (R = CF 2 SAr and 4 CFHSAr) were developed. The derivatives with R = CF 2 SAr were ob tained by both heterocyclization of 1 substituted 5 aminopyrazoles with ethyl 4,4 difluoro 3 oxo 4 phenylsulfanylbutanoate and replacement of the Br atom in 4 bromodifluoromethyl 6,7 dihydro 1H pyrazolo[3,4 b]pyridin 6 ones by sodium arenethiolates. The fragment 4 CF HSAr was introduced by replacement of the Cl atom in 4 chlorofluoromethyl 6,7 dihydro 1H pyrazolo[3,4 b]pyridin 6 ones by sodium arenethiolates. Oxidation of 4 CF 2 SPh 6,7 dihydro 1H pyrazolo[3,4 b]pyridin 6 ones gave the corresponding sulfoxides; their structures were con firmed by X ray diffraction data.Key words: pyrazolo[3,4 b]pyridines, fluorine containing 6,7 dihydro 1H pyrazolo[3,4 b] pyridin 6 ones, 1 substituted 5 aminopyrazoles, heterocyclization, fluorine containing ethyl acetoacetates, microwave irradiation, arylsulfanyl(difluoro)methyl group, arylsulfinyl(difluoro) methyl group.The pyrazolo[3,4 b]pyridine framework is a key struc tural fragment of many heterocyclic compounds showing a broad spectrum of biological activity. 1 In the last de cade, some heterocycles of this class have been found to regulate the cardiovascular system 2 and possess antiviral, 3 antitumor, 4 antiinflammatory, 5 antimicrobial, 6 and anti parasitic properties. 7 Fluoroalkyl containing pyrazolo [3,4 b]pyridines are also believed to be candidates for med ications and considered to be potential inhibitors of ade nosine deaminase and inosine 5´ monophosphate dehy drogenase. 8 Primary attention has been given to the syn thesis of CF 3 containing pyrazolo[3,4 b]pyridines 1, 9 while derivatives containing the fragment CF 2 were repre sented by CF 2 H containing pyrazolo[3,4 b]pyridines. 8 At the same time, the structural fragment CF 2 , which is ster ically similar to the CH 2 group, contrasts sharply with the latter in polarity and reactivity. 10

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Difluoromethylenephosphonates: synthesis and transformations

Cited by 23 publications

References 19 publications

Phosphonate Analogues of Arabinose 5‐Phosphate: Putative Ligands for Arabinose 5‐Phosphate Isomerases

Phosphonate Analogues of Arabinose 5‐Phosphate: Putative Ligands for Arabinose 5‐Phosphate Isomerases

The Synthesis of Novel 5′‐Deoxy‐3′,5′,5′‐trifluoro‐apiosyl Nucleoside Phosphonic Acid Analogs as Antiviral Agents

Synthesis of new fluorine-containing pyrazolo[3,4-b]pyridinones as promising drug precursors

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